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Halley Feiffer is waiting for me outside Planned Parenthood on Bleecker and Margaret Sanger Square in Manhattan. Nearby, two teenage boys, presumably waiting on teenage girls, hang awkwardly. "I'm a little scared," Feiffer says. "I'm so glad I have you here with me." We walk into the lobby, where a stern guard behind bullet-proof glass stops us. "Only one of you can come in," he says. When we explain we only want free condoms, he brightens up. "You can have as many as you like," he says, handing us two lunch bags of city-issued Lifestyles. We stuff these into even bigger bags we've brought with us, since our plan is to collect as many condoms as possible. Feiffer, best known for playing Jesse Eisenberg's girlfriend in The Squid and the Whale, wants them to promote her new film, He's Way More Famous Than You: With laborious dedication, she'll press a heart-shaped sticker with the film's title on each condom. It promises to be a long day.

Using the NYC Condom Finder app — that’s a real thing — we are next directed to Soho, skirting some construction on a sidewalk marked off with yellow tape. "Surely I can walk through here," she laughs. "They know who I am!" Although, maybe not. The premise of her film, which she calls a "feel-good comedy about alcoholism," is that Halley Feiffer, playing a hot-mess version of herself, hasn't quite reached the lower rungs of fame and must enlist actually famous people to help her make a movie about herself. In reality, Feiffer brought on Eisenberg, Ben Stiller, Natasha Lyonne, and Mamie Gummer for cameos; Ralph Macchio makes an appearance as a sex addict, hence the condoms; and Ugly Betty star Michael Urie directed.

At Housing Works on Crosby Street, rubbers (yes, rubbers) are offered in a basket right at the front counter, next to another basket filled with free lube. "No one ever takes the lubricant," one staffer sighs. After I explain Feiffer's condom needs, a volunteer worker named Tom brings up a large box from downstairs and gives her a couple hundred. "O.M.G.," Feiffer says. "I'm getting high off getting all these condoms." En route to the next location, we pass by Bowery Coffee, which has an outside sign promising "Iced Coffee, Iced Tea, and Cute Funny boys." This is an assertion that demands to be tested, so we go inside. Feiffer promptly hits it off with barista Felix (definitely cute, kind of funny) — and so we ask him if he has any condoms for us. While he goes to check, she laments that her one big scene in this year's Tribeca Film Festival entry Almost Christmas was cut down to a few seconds so that it's just "me and Paul Rudd drinking and flirting and you have no idea who I am." Before sorrow can set in, Felix returns — but with no condoms. "I guess we're all out," he says. He gives us his phone number instead.

One of our more instructive stops is at Toys in Babeland where Debbie, a helpful sales clerk, tells us that the Magnum super-size condoms are mainly a marketing strategy. Regular condoms, she says, "could fit on your head, if they had to." Feiffer rubs some vaginal moisturizer on her hands, and then I test the 50 Shades of Grey-brand blindfold on her. ("You really can't see anything!") Then, a sexy tickler. ("I don't know how turned on I would get — it's like a cat toy.") The lipstick vibrators are intriguing, but Feiffer is starting to fade.

Luckily, and rather oddly, a nearby mattress store called CoCo-Mat offers a free downstairs nap chamber in which to sample its wares. We don't have the required appointment, but a sales rep lets us borrow the room and brings us fresh orange juice. "Who knew this was here?" Feiffer marvels, looking around at the amenities (slippers, towels, a shower). "This is like my dream hotel room, even though there are no windows. It's like a safe dungeon. I would be okay with being someone's sex slave if I got to live here. How bad could it be?"

We climb under a deluxe comforter on a very expensive, all-natural bed. "I don't think this is worth $16,000," Feiffer whispers. "It's okay," I say. "We're not going to buy it." She debates texting Felix to invite him to join us: "I'm on a free bed. P.S., I have condoms." But the thought passes. When nap time is over, the store gifts us with free lavender sachets. Very nice. "This was awesome," Feiffer says. "We got condoms, and we slept together!"